[Hiring] Principal Software Engineer, AI @Jobber

Role Description

Do you want to be the first engineer on something an entire company will run on? Then Jobber might be the place for you! We're looking for a Principal Software Engineer, AI, to join the Office of the CEO.

The team:

• This is a startup inside Jobber.
• A small, senior team in the Office of the CEO with a mandate to reinvent how a 1,000-person company operates in the AI era.
• No layers between you and the decision-makers, no roadmap theater, no waiting for alignment.
• We ship something real every few hours, learn from it, and compound.
• The work touches every function at Jobber, and what we build becomes how the company thinks and moves.

The role:

• Reporting to the VP of Customer Experience Innovation, the Principal Software Engineer will be the founding technical seat.
• You'll architect and build new AI systems from zero to production.
• Own the hard problems that come with putting AI at the center of how a company runs — trust, permissions, security, and quality at scale.
• This is a builder's role with unusual range.
• One week you're designing the architecture of a system nobody at Jobber has built before; the next you're embedded with a team, shipping working AI into their real workflow.
• Make fast build-vs-buy calls, run POCs and kill them without sentiment.
• Set the technical standards that everything AI at Jobber gets held to.

The Principal Software Engineer, AI will:

• Architect and build new internal AI systems end to end, from first design to production, as the founding engineer.
• Own the hard parts of trustworthy AI at company scale: retrieval quality, permissions, security, and reliability.
• Work hands-on across the modern AI stack (LLMs, retrieval, agents, integrations) while keeping the foundations deliberately pragmatic.
• Embed with teams across the company, working day-to-day with function leaders and their teams and weekly with executive leadership.
• Drive build-vs-buy evaluations and fast POCs, with the judgment to commit hard and kill fast.
• Work directly with executive leadership: what you build informs how the company makes decisions, every day.

Qualifications

• A track record of building production systems at Staff+ scope: data infrastructure, retrieval, or applied AI used daily by hundreds to thousands of people who depend on it.
• Hands-on depth with the modern AI stack, and at least one battle scar from a system that showed you how confidently AI can be wrong.
• Pragmatic technology instincts: you reach for proven tools by default and can defend the exceptions.
• Founding-engineer, consulting, or forward-deployed experience: comfortable owning outcomes inside someone else's domain.
• A daily working relationship with AI tools and agents, as instruments you build with and build for.
• The pragmatism to ship every few weeks, the standards to make it trustworthy anyway, and the communication skills to explain both to a CEO.

Requirements

• Minimum annual salary of $229,300, a midpoint of $269,700, and a maximum salary of $310,200.
• Compensation designed to reflect the progression from learning the ropes to truly excelling.
• Base salary includes equity rewards, annual stipends for health and wellness, retirement savings matching, and an extended health package with fully paid premiums.
• Access to a dedicated talent development program that includes career coaching and opportunities for career development.

Benefits

• A total compensation package that includes an extended health benefits package with fully paid premiums for both body and mind.
• Matching in RRSP, TFSA or FHSA, and stock options.
• A dedicated Talent Development team and access to coaching, learning, and leadership programs.
• A unique opportunity to build, grow, and leave your impact on a $400-billion industry.
• A supportive and humble team that cares about customers.
• Commitment to fostering an inclusive work environment and equal opportunity employment.